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DP IB Chemistry: SL

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Home / IB / Chemistry: SL / DP / Topic Questions / 10. Organic Chemistry / 10.2 Functional Group Chemistry / Structured Questions: Paper 2


10.2 Functional Group Chemistry

Question 1a

Marks: 2
a)
Dichloromethyl benzene reacts with chlorine to produce trichloromethyl benzene. State the name of this type of menchanism and the required condition. 

[2]

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    Question 1b

    Marks: 4
    b)
    Outline the mechanism for the reaction occurring in part a).
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      Question 1c

      Marks: 1
      c)
      A reaction pathway is shown below. Compound J reacts with bromine water to form a colourless solution.

      10-2-ib-sl-sq-hard-q1c-compound-j

      State the IUPAC name for Compound J.
      [1]
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        Key Concepts
        Reactivity of alkenes

        Question 1d

        Marks: 2
        d)
        Identify the reagents and conditions for the formation of Compound Y from Compound J. 
        [2]
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          Question 2a

          Marks: 3
          a)
          Compounds W, X and Y are all carbohydrates with X and Y each containing five carbons. Compound W and a byproduct, compound Z, are formed from the reaction between compound X and YCompound X can be oxidised by the reaction with acidified potassium dichromate to give compound Y.

          2.754 g of compound
          Y contains 0.027 moles.

          Using the information given, state the name of compound
          Y and justify your answer.
          [3]
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            Question 2b

            Marks: 2
            b)
            Deduce the structural formula of compound W and explain how compound Z is formed in the reaction.
            [2]
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              Key Concepts
              Esterification

              Question 2c

              Marks: 4
              c)
              Compound X will oxidise to compound Y if allowed to fully oxidise. Explain how a student could stop the full oxidation of compound X
              [4]
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                Key Concepts
                Distillation & reflux

                Question 2d

                Marks: 1
                d)
                Deduce the formula of an isomer of compound X that will not react with acidified potassium dichromate, H+ / K2Cr2O7.
                [1]
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                  Question 3a

                  Marks: 2
                  a)
                  Ester A is responsible for a raspberry scent and has the molecular formula C5H10O2. Ester A can be produced by the reaction of an acid with a branched primary alcohol. Identify the acid and alcohol used to prepare ester A
                  [2]
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                    Key Concepts
                    Esterification

                    Question 3b

                    Marks: 2
                    b)
                    State the IUPAC name and draw the structural formula of ester A.
                    [2]
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                      Key Concepts
                      Esterification

                      Question 3c

                      Marks: 1
                      c)
                      State the name of the product when the alcohol used to form ester A reacts with potassium permanganate, KMnO4 (aq).
                      [1] 

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                        Question 4a

                        Marks: 2
                        a)
                        The following scheme shows reactions of Compound A. 

                        10-2-ib-sl-sq-hard-q4a-reaction-scheme
                        i)
                        Deduce the structural formula of compound A.
                        [1]
                        ii)
                        Apply IUPAC rules to name compound B.
                        [1]
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                          Question 4b

                          Marks: 2
                          b)
                          Reaction 1 forms an alcohol when reacted with concentrated sulfuric acid, H2SOand steam. 

                          i)
                          State the conditions required for this reaction.
                          [1]

                          ii)
                          Deduce the structure of the intermediate in this reaction. 
                          [1]
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                            Key Concepts
                            Hydration of alkenes

                            Question 4c

                            Marks: 3
                            c)
                            Butan-2-ol can also be directly formed from a halogenoalkane. 

                            i)
                            State the name of of the type of reaction occurring in this conversation.
                            [2]
                            ii)
                            State the conditions for this reaction. 
                            [1]
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                              Question 4d

                              Marks: 1
                              d)
                              Identify the structure of the repeating unit of poly(but-2-ene).
                              [1]
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                                Key Concepts
                                Polymers

                                Question 4e

                                Marks: 1
                                e)
                                Compound A reacts with hydrogen bromide to form compound C. A student suggested a possible formula of compound C is CH2(Br)CH2CH2CH3.

                                State whether the student is correct and justify your answer. 
                                [1]

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                                  Question 5a

                                  Marks: 2
                                  a)
                                  A student investigated two reactions of phenylethene, C6H5CHCH2. First she reacted phenylethene with excess bromine at room temperature to form Compound A. She then added aluminium bromide, AlBrto the reaction mixture to form Compound B

                                  Draw the structure of Compound A and identify one the isomers of C8H7Br3 formed in the second reaction. 

                                  10-2-ib-sl-sq-hard-q5a-reaction-pathway

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                                    Key Concepts
                                    Reactions of benzene

                                    Question 5b

                                    Marks: 2
                                    b)
                                    2,4,6-trinitrotoluene (TNT) can be manufactured from benzene as shown below.

                                    Chem OCR A2 6.1 Q5c

                                    5.00 g of benzene was used in step 1. Use section 6 of the data booklet to determine the theoretical yield for step 1.
                                    [2]
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                                      Key Concepts
                                      Reactions of benzene

                                      Question 5c

                                      Marks: 3
                                      c)
                                      Step 2 involves the formation of a nitronium ion for the nitration of Toluene, as shown in the following equation:

                                      HNO3 + 2H2SO4 → NO2+ + 2HSO4- + H3O+

                                      i)
                                      Explain the role of the nitric acid in the formation of the electrophile.
                                      [2]
                                      ii)
                                      Explain the role of the sulphuric acid in the overall nitration reaction.
                                      [1]
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                                        Key Concepts
                                        Reactions of benzene

                                        Question 5d

                                        Marks: 1
                                        d)
                                        Explain why the product of step 2 is most likely to have the nitro group bonded to the second or fourth carbon atom. 
                                        [1]
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                                          Key Concepts
                                          Reactions of benzene